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Self-Catalyzed Rapid Synthesis of <i>N</i>-Acylated/<i>N</i>-Formylated α-Aminoketones and <i>N</i>-Hydroxymethylated Formamides from 3-Aryl-2<i>H</i>-Azirines and 2-Me/Ph-3-Aryl-2<i>H</i>-Azirines

Aramita De, Sougata Santra, Grigory V. Zyryanov, Adinath Majee

2020Organic Letters24 citationsDOI

Abstract

A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.

Topics & Concepts

FormamidesChemistryTrifluoroacetic acidAminoketoneFormamideCatalysisArylOrganic chemistryTrifluoroacetic anhydrideAlkylSynthesis and Catalytic ReactionsFluorine in Organic ChemistryChemical Synthesis and Analysis
Self-Catalyzed Rapid Synthesis of <i>N</i>-Acylated/<i>N</i>-Formylated α-Aminoketones and <i>N</i>-Hydroxymethylated Formamides from 3-Aryl-2<i>H</i>-Azirines and 2-Me/Ph-3-Aryl-2<i>H</i>-Azirines | Litcius